1: 1.) 40percent aq. HNO3, NaNO2, 2.) concd. NH3 / 1.) ethanol, 0 deg C, 30 min, 2.) methanol, reflux 2: 72 percent / 1 h / Heating 3: 96 percent / CH2Cl2; diethyl ether / 4 h 4: 77 percent / H2 / 5percent Pd/C / acetic acid / 1 h / 2327.2 Torr 5: B2H6 / tetrahydrofuran / 2 h / Heating 6: 39 percent / 5percent Pd/C / xylene / 3.5 h / Heating View Scheme

1: 72 percent / 1 h / Heating 2: 96 percent / CH2Cl2; diethyl ether / 4 h 3: 77 percent / H2 / 5percent Pd/C / acetic acid / 1 h / 2327.2 Torr 4: B2H6 / tetrahydrofuran / 2 h / Heating 5: 39 percent / 5percent Pd/C / xylene / 3.5 h / Heating View Scheme

1: B2H6 / tetrahydrofuran / 2 h / Heating 2: 39 percent / 5percent Pd/C / xylene / 3.5 h / Heating View Scheme

1: 96 percent / CH2Cl2; diethyl ether / 4 h 2: 77 percent / H2 / 5percent Pd/C / acetic acid / 1 h / 2327.2 Torr 3: B2H6 / tetrahydrofuran / 2 h / Heating 4: 39 percent / 5percent Pd/C / xylene / 3.5 h / Heating View Scheme

1: 77 percent / H2 / 5percent Pd/C / acetic acid / 1 h / 2327.2 Torr 2: B2H6 / tetrahydrofuran / 2 h / Heating 3: 39 percent / 5percent Pd/C / xylene / 3.5 h / Heating View Scheme

iron in ethanol; acetic acid Ambient temperature1.) 2 h at room temperature,2.) 0.75 at 80-90 grad C;

palladium on activated charcoal in xylene 3.5 h; Heating;

palladium on activated charcoal in xylene Heating;

1: 64 percent / 48percent aq. HBr / 15 h / 95 °C 2: 1.) 40percent aq. HNO3, NaNO2, 2.) concd. NH3 / 1.) ethanol, 0 deg C, 30 min, 2.) methanol, reflux 3: 72 percent / 1 h / Heating 4: 96 percent / CH2Cl2; diethyl ether / 4 h 5: 77 percent / H2 / 5percent Pd/C / acetic acid / 1 h / 2327.2 Torr 6: B2H6 / tetrahydrofuran / 2 h / Heating 7: 39 percent / 5percent Pd/C / xylene / 3.5 h / Heating View Scheme

1: 84 percent / aluminium oxide (activated, basic) / 3.5 h / Ambient temperature 2: 36 percent / Aluminium oxide (activated, basic) / benzene / 1 h / Heating 3: 89 percent / Iron powder / acetic acid; ethanol / Ambient temperature; 1.) 2 h at room temperature,2.) 0.75 at 80-90 grad C View Scheme